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AISF

CAS 2172794-56-6, Cat. No EN300-6745900
Sulfofluorination reagent

4-(Acetylamino)phenyl]imidodisulfuryl difluoride, schema
4-(Acetylamino)phenyl]imidodisulfuryl difluoride, AISF

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Fluorosulfates have a variety of applications in organic synthesis acting like a pseudo-halogen in a wide range of Pd-catalysed cross-coupling reactions1,2. They are also used as tool compounds in proteomics. AISF is stable under normal conditions but a crystalline substance, soluble in THF used for sulfofluorination of phenols and amines3. This reagent is a good alternative to hazardous SO2F2 which possesses greater selectivity and is much easier to handle than gaseous sulfuryl fluoride. The reaction happens at room temperature, and it takes minutes for sulfofluorination to happen on a diverse scope of substrates. Moreover, great chemoselectivity was observed, AISF may be used in the presence of anilines, primary and secondary alcohols as well as carboxylic acids that leave unaffected2,4.

Synonyms: 4-(Acetylamino)phenyl]imidodisulfuryl difluoride

Selected publication

  1. Palladium in Cephalosporin Chemistry: An Inexpensive Triflate Replacement for Palladium Acetate Mediated Coupling Reactions.

    Roth G.; Sapino C. Tetrahedron Lett 1991, 32 (33), 4073–4076. DOI: 10.1016/S0040-4039(00)79866-2

  2. Arylfluorosulfates Inactivate Intracellular Lipid Binding Protein(s) through Chemoselective SuFEx Reaction with a Binding Site Tyr Residue.

    Chen W.; Dong J.; Plate L.; Mortenson D.; Brighty G.; Li S.; Liu Y.; Galmozzi A.; Lee P.; Hulce J.; Cravatt B.; Saez E.; Powers E.; Wilson I.; Sharpless K.; Kelly J. J Am Chem Soc 2016, 138 (23), 7353–7364. DOI: 10.1021/jacs.6b02960

  3. [4‐(Acetylamino)Phenyl]Imidodisulfuryl Difluoride.

    Carneiro S.; Ball N.; Lee J.; Ende C. am. Encyclopedia of Reagents for Organic Synthesis 2021, 1–3. DOI: 10.1002/047084289X.rn02400

  4. Introduction of a Crystalline, Shelf-Stable Reagent for the Synthesis of Sulfur(VI) Fluorides.

    Zhou H.; Mukherjee P.; Liu R.; Evrard E.; Wang D.; Humphrey J.; Butler T.; Hoth L.; Sperry J.; Sakata S.; Helal C.; am Ende C. Org Lett 2018, 20 (3), 812–815. DOI: 10.1021/acs.orglett.7b03950

 

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